(2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene

Base Information

Chemical Name:(2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene
CAS No.:377750-99-7
Molecular Formula:C₂₅H₃₈O₆
Molecular Weight:434.573
Hs Code.:

Synonyms:(2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene

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Chemical Property of (2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene

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Technology Process of (2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene

There total 7 articles about (2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

: 3282-30-2
pivaloyl chloride

: 377750-98-6
(2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-2-octen-1-ol

: 377750-99-7
(2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene

Guidance literature:: With triethylamine; In pyridine; at 0 ℃; for 2h;
DOI:10.1021/ol016449u

Reference yield:

: 88406-01-3
2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol

: 377750-99-7
(2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 93 percent / dimethylformamide / 2 h / 0 °C

2.1: BH₃*SMe₂ / tetrahydrofuran / 2 h

2.2: 77 percent / aq. H₂O₂; NaOH / tetrahydrofuran; ethanol / 3.5 h

3.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 616 mg / benzene / 14 h / 20 °C

5.1: 97 percent / DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

6.1: 97 percent / Et₃N / pyridine / 2 h / 0 °C

With oxalyl dichloride; dimethylsulfide borane complex; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3.1: Swern oxidation / 4.1: Wittig reaction;
DOI:10.1021/ol016449u

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 377750-99-7
(2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 93 percent / dimethylformamide / 2 h / 0 °C

2.1: BH₃*SMe₂ / tetrahydrofuran / 2 h

2.2: 77 percent / aq. H₂O₂; NaOH / tetrahydrofuran; ethanol / 3.5 h

3.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 616 mg / benzene / 14 h / 20 °C

5.1: 97 percent / DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

6.1: 97 percent / Et₃N / pyridine / 2 h / 0 °C

With oxalyl dichloride; dimethylsulfide borane complex; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3.1: Swern oxidation / 4.1: Wittig reaction;
DOI:10.1021/ol016449u